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More Christmas Shopping

December 22, 2017


It finally happened.

I will define probability as a measure of the likeliness of some event happening if you tried once.  Therefore, if you try multiple times, the probabilities add up.  Eventually, the event will happen…  You know, like getting caught while crossdressed in public.

Oh, speaking of being crossdressed in public, I went on an outing recently.  I had to do some Christmas shopping.  It was “far enough” from home that I decided to make an outing of it.  I wanted to wear another Christmas outfit.  This was my third outing in Christmas colors!  I brought a brush stroke abstract patterned, black and white, stretchy skirt that came to below my knees.  For up top, I brought a red pull over long sleeved shirt.  Over that, I had an unbuttoned, white collared shirt.  For below the skirt, I had shiny off black pantyhose and black flats.  I thought the outfit looked very nice.  I felt good about myself when I wore it.


I felt some unease about going shopping in the town I was headed to because it was not unreasonable that people who know me might travel this far to do their shopping as well.  In fact, this town might be the closest town to shop in for some people I know.  It was a greater risk.  I decided to weigh the risks at each stop.

Department Store
My first stop was to a rather large department store.  I figured that it was too crowded to risk going in a skirt.  I put on the shoes, and the two tops, but I kept on my mens blue jeans.  I entered the store and did my shopping.  I doubt anyone noticed anything unusual about me.

For supper, I went to a restaurant that I have been to before in menswear.  The parking lot was almost empty.  I put on the skirt.  Inside, there were two tables with customers at them.  In an unlit area of the restaurant, there were two women eating.  One of those women got up and seated me.  I recognized her.  I have seen this woman before in another restaurant in this chain.  I asked her if she was the owner.  She said her father was.  She said that they own four locations.  So now, I have crossdressed in two of her restaurants!  However, this was the first time she had ever seen me dressed up.  I told her my name and she told me hers.  She offered me her hand and we shook hands  She was very kind and welcoming.

I ate my food without incident.  Then I got up to pay.  The woman was still sitting with her friend.  She saw me leaving and she called me by name and told me good-bye.  I paid my bill and left.

My nervousness had diminished.  I was starting to feel safe…

Sporting Goods Store
I drove to a sporting goods stores to get a gift for my daughter.  I had it on hold.  I toured the store for a little while before asking for help.  I looked at everyone in the store and made sure there was no one there whom I knew.  I was still wearing my pretty skirt.

I told the girl who was working at the cash register that I needed help getting the item I had on hold.  She phoned someone asking for assistance for my needs.  While she was on the phone, she looked down at my skirt for a second.  Then she looked down down to my legs and feet.  She looked there for a few seconds.  Then she looked back to my face and elsewhere in the room.  She hung up and said that someone was coming to help.

A man arrived to help me.  He took me to the item.  It was near the cash register area.  He did some inspections on the item.  He showed me some aspects of the product.  He spent a significant amount of time with me.

At one point, I saw another man in the same area.  I was surprised to realize that I knew him!  He was someone I had occasional dealings with over fifteen years ago.  I did not know his name, but we recognized each other.  I had several thoughts, “Did he see me before this?  I was not paying attention.  What do I say?  Should I hide?”

I do not know this man very well.  I have only seen him on one occasion in the last fifteen years.  He and I spoke a little on that occasion.  He is a nice guy.  I said, “Hey.”  (Only one second may have passed between the moment I recognized him and me saying, “Hey”.)  He acknowledged me with his face, but he continued walking.  He did not smile.  I wondered if he had already seen my outfit.  I was not in full view to him at the moment.  I moved a little so that a rack blocked all of me from the man.  The employee was still helping me.

I was intrigued by the fact that I was not very frightened.  I was mostly annoyed with myself for taking such a foolish risk.  After a couple minutes, I moved some so I could see where the guy had been.  He was gone.  He was no longer in the area.  I was pleased with that.

Eventually the employee, who never showed any interest in my outfit, finished.  He walked with me toward the cash register and gave some instructions to the girl.  That is when the guy I knew came back into the store.  Apparently, he had exited when he had disappeared.  He came into the store and walked right by me, picked up his selections, and got in line behind me.

So, I said, “Hello” again.  He said, “Hello” in reply.  I told him to go ahead of me because my purchase would take some extra time.  He commented as he passed, “That dress you are wearing is fabulous.”  Alright, now I have two things I want to talk about…  That is my second “fabulous” in one month.  I do not know if he was being serious or if he was just pointing out the “elephant in the room” (a euphemism that means a secret or truth that everyone in the room knows about, but they might feel uncomfortable mentioning).  Maybe he was just wanting me to feel comfortable.  Maybe he also crossdresses.  Who knows?

I was feeling scared, annoyed, and embarrassed.  I was not ready for this.  I should have made a sheepish expression with my face and said, “…no one was supposed to see me this way…” or “I’m a little embarrassed about this.”  Hopefully then he would have known that this is not public knowledge.  At least I should have smiled and said, “Thank you.”  Instead, I think I just awkwardly bobbed my head and looked away.

He placed his items in front of the cashier.  She started ringing up his selection.  I asked him, “Are you going fishing?”  He replied with a story about his family member who has taken up professional fishing.  I replied with my own story of a semi-professional sport fisherman that I know.  He finished his transaction and we said our good-byes.

Then, I finished my purchase and I left the store.

Ice Cream Shop
One might expect that I would have been rather shaken up by this.  Apparently not.

I went to an ice cream shop and bought a small bowl of ice cream.  I sat at a table and ate it.  The employee probably never saw my outfit.  A couple were in the restaurant eating.  They guy saw me and paid some attention to me, but she never looked my way.

Small Store
I went to small store.  I shopped for a few minutes to find some birthday wrapping paper.  There were a lot of employees working in the store.  Eventually, I got in line.  The two young women behind the counter had seen me in the store.  I think enjoyed getting an opportunity to talk to me.  Of course, my clothing was never mentioned.  I asked if they had a specific candy I could not find.  One hurried around the counter to help me.  The girl behind the counter suggested an alternative.  The second employee came back around the counter and stayed with the girl running the cash register.  We all said good-bye and Merry Christmas after my transaction.  Then I left.

Busy Store
The next store I went to was busy enough that I decided to put back on my blue jeans.  I am glad I did.  I would have felt uncomfortable there.  I ended up needing help.  I do not think anyone noticed anything unusual about my shirts or shoes.

Large Discount Store
My “last stop” was a large discount store.  I did not wear my skirt there either.  I did my shopping and again, I think no one noticed anything unusual about me.  (I wish I had thought to bring my ladies’ blue jeans.)

Fast Food
My actual last stop was at a fast food restaurant.  I put back on my skirt and stopped to get a milkshake.  I walked into the restaurant and went straight to the counter.  There was only one family eating in the restaurant.  I had to wait briefly.  A woman who was older than me got in line behind me.  I placed my order.  Then I waited.  The woman had to wait a long time to place her order.  We looked at each other at one point and shared a momentary facial acknowledgement of, “Why is this taking so long?”

A man and his wife got in line behind us.  We all waited.  Eventually my milkshake came and I left.

So now, I do not know what will come of this.  I do not know if the guy I saw even remembers my name.  I do not remember his.  There is a slight chance that we will see each other again around town.  To my knowledge, we do not have any shared acquaintances.  I really do not expect much to come of this.

I am not sure how to take my second “fabulous”.  I was wearing a skirt, not a dress.  How much weight should I put on such a compliment?  These are uncharted waters, as they say…

So, now I know what it feels like to be caught in public while crossdressed.  It is a helpless feeling.  However, it was no more dramatic than just another person seeing me.  I kind of think of this as a non-event, but I know intellectually that I should not.  The “bottom line” is this: I need to become more conservative about where I go out in public.  I am obviously becoming too sloppy if I want to keep this a secret from my friends and family…


From → True Stories

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  1. Long Lunch Crossdressed | joeypress

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